Understanding your audience's objectives is one of the most critical yet frequently overlooked aspects of building a successful business case. Too many managers fall into the trap of believing their project's benefits are self-evident, assuming that a strong ROI calculation or an elegant technical solution will automatically win approval. However, The HBR Guide to Building Your Business Case by Raymond Sheen teaches us that this assumption is fundamentally flawed. Your stakeholders are looking for projects that directly support their strategic priorities, and they'll reject even brilliant ideas that don't clearly align with what they're trying to achieve.

Think of your business case as a key that must fit a very specific lock. That lock is shaped by your organization's strategic priorities, your stakeholders' personal objectives, and the pressures they face from their own bosses and boards. As the guide emphasizes, "Senior leaders are looking for projects and initiatives that fit the company's strategy, and they're likely to reject those that don't." This fundamental truth means you must become a detective, uncovering what truly matters to your decision makers and then explicitly demonstrating how your project helps them achieve those goals.

Annual reports and CEO communications reveal the exact language, priorities, and metrics your stakeholders care about. The best way to gain support is to explicitly demonstrate how your idea supports the company's stated priorities. Don’t assume stakeholders will connect the dots themselves—draw those connections clearly and repeatedly.

Carefully review recent annual reports, CEO messages, and other official communications for recurring themes and key phrases. For example, some organizations may emphasize customer satisfaction, while others focus on innovation or operational efficiency. Projects that do not clearly tie into these dominant themes are often deprioritized or rejected.

Document these themes word-for-word. If the CEO highlights "digital transformation" as a top priority, use that exact phrase in your business case. This signals alignment and shows you understand what stakeholders are accountable for. Even renaming your project to reflect strategic language can increase engagement.

Also, align your business case with published metrics and targets. If the annual report sets goals like 15% revenue growth or a 2% margin improvement, show how your project will contribute to those numbers. Stakeholders want to see a direct line between your proposal and the outcomes they are measured on. Quantifying your impact in these terms makes your project essential, not optional.

While annual reports provide the official strategic narrative, you need to understand how individual stakeholders interpret and act on these priorities. The HBR Guide recommends approaching stakeholders with three essential questions that cut through corporate speak to reveal what really drives their decisions:

• What are your group's chief objectives this year?
• How do you measure success?
• What are your barriers?

The power of these three questions lies in their ability to reveal the gap between official strategy and operational reality. A stakeholder might tell you their official objective is "digital transformation," but when you ask how they measure success, they might reveal they're actually evaluated on cost reduction and system uptime. Moreover, when you probe about barriers, they might confess that previous transformation attempts failed due to inadequate change management, making them skeptical of ambitious technology projects.

Consider this conversation between a manager preparing a business case and a key stakeholder:

• Jessica: Thanks for meeting with me, Victoria. I wanted to understand your team's priorities before finalizing our warehouse automation proposal. What would you say are your chief objectives this year?
• Victoria: Well, officially we're focused on digital transformation—that's the big company initiative. We need to modernize our operations.
• Jessica: That makes sense. How does your team measure success for digital transformation?
• Victoria: To be honest, what really matters at the end of the day is cost reduction. My performance review is based on cutting operational costs by 12% this year, not on how many systems we digitize.
• Jessica: That's helpful to know. What barriers are preventing you from achieving that 12% reduction?
• Victoria: Our biggest challenge is that the last two technology projects went 40% over budget and delivered half the promised savings. The board is skeptical of any new tech investments now. They keep asking if we really need new systems or if we should just optimize what we have.
• Jessica: So you're caught between the company's push for digital transformation and the board's concern about technology investments not delivering cost savings?

Stakeholders must justify their decisions to their own bosses, boards, and teams. Even if the people reviewing your business case have decision-making authority, they will still need to defend their choices when actual revenues and costs start rolling in. This means you need to equip your reviewers with clear arguments and evidence they can use to support your proposal to others higher up the chain. Think about the layers of accountability: a VP answers to the COO, who answers to the CEO, who answers to the board. Each level has different concerns and language. Keep in mind that when you present your case to a CEO, they will likely be thinking ahead to how the board of directors will react and what concerns they might raise.

To help, create "elevation-ready" content—executive summaries, financials, and strategic points that can be easily reused in higher-level presentations. One IT manager succeeded by providing a one-page "Board Brief" using language from board meetings, making it easy for the CIO to sell the proposal upward.

Anticipate political dynamics and be aware of past failures. If the board is wary of failed projects, acknowledge this and explain what’s different now. Stakeholders must "justify their choices when actual revenues and costs start rolling in," so be sure to provide realistic projections and clear metrics to help them defend the decision long-term.

In the upcoming role-play sessions, you'll have the opportunity to practice these techniques in realistic scenarios, engaging with simulated stakeholders to uncover their true objectives, success measures, and barriers. You'll learn how to ask the right questions, listen for what matters most, and tailor your business case language to echo strategic priorities. By applying these skills, you'll be able to craft business cases that not only align with organizational goals but also empower your stakeholders to champion your proposal with confidence.